Private Trip Planning & Concierge Services

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Everything on this site is free to read. Some of it — the restaurant you can't get a table at, the Palio window you can't book directly, the estate that only takes visitors through an introduction — takes a phone call and a relationship to actually arrange. That's what this is for.

If that's what you're after, our editorial guides above already cover the same ground for free — this is for when you want us to do the arranging instead of just the recommending.

What We Arrange

Restaurant reservations at tables that don't take walk-ins. Several of the addresses in our dining guides — Osteria Le Logge among them — run fully booked weeks out, particularly around the Palio. We know which tables are worth wanting — and the honest way to ask for them.

Palio viewing. Balcony and window places for the Palio are scarce, private, and priced accordingly. We'll tell you honestly what is realistic for your dates — and what isn't.

Private wine estate visits. Introductions to estates that don't take unannounced visitors, including smaller Chianti Classico and Brunello producers not set up for casual tasting-room traffic.

Villa and property viewings. For readers exploring a Tuscan property purchase — see our guide on buying property in Tuscany — we can arrange viewings and introduce vetted local agents and independent lawyers. We don't sell property or take a commission on it; we make the introduction.

Full itinerary curation. A private driver, a sequenced multi-day plan across Siena, Chianti, and the Val d'Orcia, restaurant bookings woven in — built around what you've actually told us you want, not a template.

How It Works

1. Inquiry. Tell us what you're planning and when — email us at concierge@sienatoscana.it with dates and a short brief. There's no charge to inquire.
2. Consultation. We respond within two business days with what's realistic for your dates and what it would involve.
3. Booking. For confirmed reservations, itineraries, and chauffeur-driven days, write to bookings@sienatoscana.it. We handle the bookings, introductions, and logistics directly with our partners.

Pricing

Single arrangement (one reservation, one introduction, one Palio viewing spot): a flat consultation fee, confirmed with you before any work begins, plus the cost of whatever's being booked.

Full itinerary curation: priced per trip, based on length and complexity — provided as a fixed quote after the initial consultation, not an hourly rate with an unpredictable final bill.

We don't publish a rate card, because the range between "book us one dinner" and "plan a nine-day trip with a driver" is too wide for one to mean anything. Every quote is confirmed with you in writing before you commit to anything.

We may earn a commission through some of our partners when arrangements are booked through us. It never affects what we recommend — the same principle that governs every editorial recommendation on this site.

Who This Is For

Readers who've found something specific in our guides and want help actually securing it — not a general-purpose travel agency service, and not a fit for last-minute requests inside 48 hours, which our partner network generally can't accommodate.

Continue Reading

• Where to Stay for the Palio di Siena
• Buying a Home in Tuscany
• Best Wineries Near Siena

Frequently Asked Questions

Is there a charge just to ask a question? No — the initial inquiry and consultation are free. You'll always know the cost before any paid work begins.

Can you get me a table at a fully booked restaurant? Often, yes, particularly with advance notice — we hold relationships with several venues in our dining guides that don't take public walk-in reservations during peak periods.

How far in advance should I inquire? As early as possible, and at minimum several weeks out — Palio-period bookings in particular should be arranged months ahead, not days.

Do you charge a percentage on property viewings or purchases? No — we make introductions to vetted agents and independent lawyers for property matters but don't take a commission on property transactions themselves.

By the Siena & Toscana editors

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Ready to enquire? Email concierge@sienatoscana.it with your dates, what you'd like arranged, and any budget indication. For confirmed bookings and itineraries, write to bookings@sienatoscana.it. We reply within two business days.